PE(19:iso/15:0cyclo) (PAMDB003918)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003918
Identification
Name: PE(19:iso/15:0cyclo)
Description:PE(19:iso/15:0cyclo) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(19:iso/15:0cyclo), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one cis-9,10-Methylenetetradecanoic acid to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-17-methylocatdecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoethanolamine
  • 1-17-methylocatdecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoethanolamine
  • GPEtn(19:0/15:0)
  • GPEtn(34:0)
  • PE(19:0/15:0)
  • PE(34:0)
  • Phophatidylethanolamine(19:0/15:0)
  • Phophatidylethanolamine(34:0)
Chemical Formula: C39H76NO8P
Average Molecular Weight: 717.9964
Monoisotopic Molecular Weight: 717.530854925
InChI Key: LTLJNWJLDIGSCA-BVYUPHKZSA-N
InChI:InChI=1S/C39H76NO8P/c1-4-5-25-35-31-36(35)26-21-17-15-19-23-28-39(42)48-37(33-47-49(43,44)46-30-29-40)32-45-38(41)27-22-18-14-12-10-8-6-7-9-11-13-16-20-24-34(2)3/h34-37H,4-33,40H2,1-3H3,(H,43,44)/t35?,36?,37-/m1/s1
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy((2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid
SMILES:CCCCC1CC1CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCCN
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent Phosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.29e-05 mg/mLALOGPS
logP7.88ALOGPS
logP10.4ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity198.25 m3·mol-1ChemAxon
Polarizability87.83 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Hydrogen ion + PS(19:iso/15:0cyclo) > PE(19:iso/15:0cyclo) + Carbon dioxide
PE(19:iso/15:0cyclo) + PG(15:0/14:0(3-OH)) > Ethanolamine + CL(15:0cyclo/15:0cyclo/14:0/19:0cycv8c)
PE(19:iso/15:0cyclo) + PG(15:0cyclo/14:0(3-OH)) > Ethanolamine + CL(15:0cyclo/15:0cyclo/19:0cycv8c/14:0)
PE(19:iso/15:0cyclo) + PG(15:0cyclo/14:0(3-OH)) > Ethanolamine + CL(15:0cyclo/19:0cycv8c/15:0cyclo/14:0)
PE(19:iso/15:0cyclo) + PG(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/19:0cycv8c/15:0cyclo)
PG(14:0(3-OH)/15:0cyclo) + PE(19:iso/15:0cyclo) > Ethanolamine + CL(19:0cycv8c/15:0cyclo/14:0/15:0cyclo)
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9030100200-b752e08279622bf98f03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9130001000-7d75c1d643ea6ba710f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9332000000-2cbadf0924cae42704c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9030100200-b752e08279622bf98f03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9130001000-7d75c1d643ea6ba710f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9332000000-2cbadf0924cae42704c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-0190201100-ccacd7a6d6ed54a945eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-4390100000-e45df1800dd778727effView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-c4e3bbba34fbef1e08f6View in MoNA
References
References:
  • Casadei MA, Ma?as P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72. Pubmed: 12450817
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
• Phosphatidylserine decarboxylase proenzyme
General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:
psd
Locus Tag:
PA4957
Molecular weight:
32 kDa
Reactions
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).

Transporters

Protein Details
• Probable phospholipid ABC transporter permease protein mlaE
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Locus Tag:
PA4455
Molecular weight:
28.4 kDa